3-Methyl-4-octanolide

The Quercuslactone (from the Latin quercus " oak " ) are organic chemical compounds found in alcoholic beverages such as whiskey, sherry and brandy and others. Therefore they are also called " whiskey lactones ".

Isomerism

They occur in four stereoisomeric configurations (3R, 4R ) and ( 3S, 4S ) (both substituents in the cis position ) and ( 3S, 4R ) and ( 3R, 4S ) (both substituents in trans position ) that is, in the form of two pairs of enantiomers, each having a different optical activity ( see below in the box).

The substituents are in the 3-position and the methyl group in position 4, the n- butyl group at the γ -butyrolactone ring; by newer nomenclature, these are the 4 - and 5-position.

Properties

Depending on the configuration, the compounds have different sensory properties. The two cis- isomers in this case have a ten times lower odor threshold than the two trans isomers.

3-methyl -4- octanolide β -methyl- γ - octalactone 5 -butyl -4- methyldihydro -2 (3H )-furanone 5 -butyl -4- methyloxolan -2-one (IUPAC) 5 Butyldihydro - 4 - methylfuran -2 (3H )-one

Formation

Quercuslactone arise from the storage of wine and spirits in oak barrels.